


Out of Options

by Jade_Dragoness



Category: Supernatural
Genre: Bobby in Hell, Community: trope_bingo, Demons, Dubious Consent, Episode: s08e19 Taxi Driver, Hell, M/M, Protective Bobby Singer, Sam and Dean are his boys, Trope Bingo Round 2, indecent proposal, sexual extortion
Language: English
Status: Completed
Published: 2013-09-13
Updated: 2013-09-13
Packaged: 2017-12-26 11:03:36
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,700
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/965192
Author URL: https://archiveofourown.org/users/Jade_Dragoness/pseuds/Jade_Dragoness
Summary: <blockquote class="userstuff">
              <p>Bobby's been in Hell for three months when Crowley appears in his cell.</p>
            </blockquote>





	Out of Options

**Author's Note:**

> Sticking this under the prompt: indecent proposal for Trope Bingo. 
> 
> Also, clearing up that nothing explicit is shown 'on screen'. Mature rating is for the dub-con (possibly non-con, ymmv) and sexual extortion.

Hell is surprisingly boring, Bobby finally decided after three months of it. That was something he sure as hell – no pun intended of course – hadn't been expecting when his Reaper had left him behind in his cell looking oddly apologetic for doing so. Which, in retrospect, had been _weird._

And that had only been the start of his oddball afterlife and he wasn't even counting his stint as Casper. Having seen the effects their times down under had had on his boys, Bobby fully expected the soul warping torture to start up pretty much as soon as he'd realized he hadn't made it up to Heaven. Not that he'd been expecting Heaven. Considering the mess those angels had on their plates the idea of oblivion, of just burning out of existence, and not ending up having to deal with those celestial dicks had actually come to grow on him. A little.

Anyway, upon realizing his bastard of a Reaper had left in him in the clutches of demons Bobby had sworn a blue-streak and braced himself for the sharp knives, broken bones and God only knew what else. 

Only nothing happened. For days and days on end he was left alone.

Frankly, it worries at him, the lack of infernal attention, because it made him think that the bastards are getting creative in plotting what they'll do to him and that the torture will start up as soon as he let down his guard just to make it that much worse. The expectation of pain makes him tense up at every distance scream and twitch at every suffering groan he hears from his neighbors. He ain't the type of man to toot his own horn and while he doesn't consider himself to be near the same category of hero as Dean and Sam (who have pissed off and gotten all of Hell after them... damn, he's proud of his boys), but he sure ain't Joe Schmoe either. He'd killed more than a handful of demons and he's lost track of how many of those black-eyed bastards and red-eyed bitches he'd sent down to Hell over his lifetime of hunting.

He kinda expected to see a few of those demons showing up with chips on their shoulders to take out their grievances on his spleen or whatever internal organ they wanted to rip out of him.

Only he got squat. Demons wouldn't even look at him. Like the one that was currently passing his cell door.

Bobby glowered at a demon wearing the body of a sweet looking redheaded girl. She passed by him, not even bothering to spare him a glare as she dragged behind her another tormented soul. At the sight of the whimpering soul Bobby had to suppress a wince, he couldn't even tell what gender it was, it was so mutilated. 

He watched as it wiggled, made breathy high-pitched noises and left behind a gory trail of blood and... pieces.

“Goddamn,” Bobby said to himself, wondering if he'd end up in the hands of whatever had done that.

“More liked God damned, but then that's the point.”

Bobby spun around as soon as he heard the voice coming from _inside_ his cell, all his hunting instincts flaring up as he tensed to attack that it took a moment for the familiarity of that smug, English-accented voice to filter through. 

Crowley's smirk was as smugly superior as ever. 

“Still attached to your red-neck chic, I see,” Crowley drawled, as he looked Bobby up and down from the tip of his boots to the trucker hat and back down again. Crowley tsked in disapproval. “You may have died in such an unfashionable ensemble, Bobby Singer but there's no need to retain the look once you're dead. Really.” He shook his head in exaggerated disappointment.

“Crowley,” Bobby said, stiffly. “What are ya doing here?” As soon as the words were out of his mouth, Bobby wished he could take them back. He didn't actually want to know what the bastard had in store for him. 

“King of Hell, remember? I hope that bullet to your crown didn't scramble your brains too much, after all, that's my job,” Crowley's smirk widened as he took several steps toward Bobby. 

Without thinking, Bobby backed up until he ran into the door of his cell. 

“Bobby, Bobby, Bobby,” Crowley drawled, amusement brightening his eyes with pleasure. “You look like you aren't happy to see me.”

Irritated, scared and too annoyed to back down even knowing that he couldn't do anything to get out of Crowley's clutches, Bobby glared back. “Ya think?” he asked sarcastically.

Crowley stopped well within Bobby's personal space without actually touching him. “You haven't been enjoying my hospitality? Really, Robert, I would have thought you'd be grateful to have been skipped over for the burning pits, and other –” Crowley twirled his forefinger in the air if to encompass the whole range of torture which Hell provided. “– nasty bits. Not many people get out of meeting the welcoming committee.”

Bobby eyed him, his mind working furiously to figure out Crowley's angle. “I flattered,” Bobby said in the driest tone he could manage. And it suddenly hit him, that maybe the reasons that the demons hadn't been showing up was because the Big Kahuna had called dibs. “Why are you really here, Crowley?”

“Oh, just killing some time, checking up on my kingdom,” Crowley said, his tone lazy and dismissive as the humor dropped from his expression. The demon tilted his head and stared at Bobby in an unblinking way which drilled into him for several seconds. Bobby bore it stoically. “I'm surprised... I had a bet with myself that you'd be asking about Moose and Squirrel within the first minute. When you last saw them they were about to launch their attack on Dick Roman. You aren't curious about their fate, at all?”

Bobby stiffened his jaw. “I haven't been here long enough.” He'd done the math ages ago. He'd been down in Hell for three months which worked out to about half a day on Earth. Topside, Sam and Dean would still be either putting the finishing touches on their plan, or they'd have settled down to snatch an hour of so of sleep before the big showdown. At least, if they weren't being idjits they'd be resting. 

Bobby fretted over them for several seconds. The longing to be back with his boys so that he could watch their backs was so intense that he briefly forgot he was in a locked cell with the King of Hell. 

“There it is,” Crowley purred, his breathe hot, humid and disturbingly minty against Bobby's face. “The concern and love you have for those boys... really, it's touching, mostly nauseating, but touching.” He touched the breast of his bespoke suit jacket over his heart in a mocking gesture.

Bobby gritted his teeth and glared, determined not to give the demon any more ammunition. “What do ya want?”

“Ooh, right down to business.” Crowley smiled. “Yes, let's get that settled first. Then we can move on to the pleasure.”

Before Bobby could fully absorb the worrying implications of that sentence, Crowley snapped his fingers.

*-*-*-*

When they reappeared Bobby jerked and nearly fell off the plush black leather chair he was on. Crowley was sitting on a large, high-backed chair which looked like a throne than anything else. Bobby took in the large room with a swift glance, taking stock of the exits (none), the weapons (quite a lot actually) which were mounted on the walls and the surprisingly large number of books on shelves behind the desk which spanned the entire wall from ceiling to the floor. The place was decorated in wood, ivory and leather.

Bobby took another look at the decorative touches. Scratch that. Wood, bone and tanned _human_ skin. Jesus, some of the skins had tattoos on them. Holding back his disgust, he forced himself to memorized the positions of everything and anything he could use should an opportunity for escape present itself. If John Winchester could get himself out of Hell then he could damn well do the same or his name wasn't Bobby Singer. He wasn't about to be upstaged by that sonuvabitch.

“I have a deal for you.”

Bobby jerked his eyes back to Crowley. His eyes widened. “Ya gotta me kidding me!” he protested, honestly bewildered and annoyed at being jerked around. “I'm already in Hell. It ain't like I can put out a second mortgage on my soul.”

“No, you're right. I do own your arse,” Crowley smirked. “Maybe deal is too strong a word. This is more like an arrangement. A proposal, if you will.”

Bobby crossed his arms and glowered, not saying a word. Whatever mind game Crowley was playing, he wasn't taking part. No way in hell!

Crowley's smile faded and his leaned back into his throne chair. His expression became thoughtful. “You know, I have the utmost confident in those Winchesters.”

Bobby blinked taken aback by the topic change. He remained wary.

“They've taken down some majorly big fish in their time, Lucifer, Michael, Azazel, Eve, just to name a few. So when it comes to prize match fights, I put my bets on those underdogs. And I've done the same for this battle royale.” Crowley leaned forward. “In fact, I've bet my kingdom.”

Bobby snorted, not particularly impressed. “That's because you know that as soon as the Leviathans have humanity under their control they'll be coming after you for dessert.”

“Yes, yes,” Crowley waved his hand dismissively. “My point is that I have complete confidence in those boys. In fact, I'm planning on throwing a fucking party to dance on Dick Roman's grave.” Crowley stood up and turned behind him to pick up a crystal tumbler and a bottle of whiskey. He raised up a second glass in silent inquiry at Bobby, who glared. “Just as well, you drink rotgut and like it. You wouldn't appreciate the craftsmanship that went into this.” Crowley a slip, a blissful expression on his face. “That's the stuff.”

“Get to the point, Crowley.”

Crowley tilted his head and walked around the desk to sit on the desktop in front of Bobby. He held up his forefinger, took another mouthful of whiskey and hummed with satisfaction, before he set the tumbler beside him. “The point...well, let's just say a thought occurred to me. Sam and Dean are disturbingly good about killing their enemies, won't you agree? A lifetime of playing Destroy All Monsters have left them with a skill set that just can't be beat. So, I asked myself: Self, after they bring down the Leviathan King, why would I risk letting those two numbskulls live to set their sights on me?”

Bobby jumped to his feet, his hands in tight fists, rage flooded through his veins. He opened his mouth to shout – to threaten – because of that smug sonuvabitch thought he could threaten _his_ boys–!

Crowley made a swift, abrupt gesture with his right hand. 

Bobby slammed back into the chair as if held in place with invisible chains, and to his mounting anger, discovered his voice had crapped out on him. He glared hotly. 

Crowley leaned forward, fascination writ all over his face as Bobby fumed. After a moment of study, he said softly, “You know it would be remarkable easy.”

Bobby growled silently in protest and his fists itched to pummel Crowley into paste.

“Well, easy may be stretching the truth a tad, but it would be easier than any other time. You see, those Winchesters have a nasty, lazy habit of not watching their backs when they go after big time monsters. They get tunnel vision. Sure, they'll be on high alert, and prepared to fight for their lives but... Sam and Dean are going after Leviathans. They wouldn't be expecting demons at their heels waiting to attack. So no holy water, devil's traps and salt lines.” The smile on Crowley's face was cruel and knowing. “And most importantly, no Bobby Singer to watch their backs.” 

A cold, heavy feeling of dread settled in Bobby's gut.

Crowley leaned closer and whispered. “And in that moment when they succeed... when they have defeated their enemy and they are the _happiest_ they could be, when they've lowered their guard because they've _won_ and saved everybody... that's when I'll strike them down and soak the room with their blood.”

Horror froze Bobby in place more thoroughly than Crowley's binding spell. The mental images – nightmares – that played in his mind at the demon's words were vivid and... all too real of a possibility.

His boys... they wouldn't expect it. Dean and Sam would be butchered.

“Unless...” Crowley added slowly, extending the word.

Bobby focused on Crowley, who was staring at him, not smiling but with an intent, predatory expression. For a moment, Bobby hated himself for falling into the demon's verbal trap. He knew exactly what Crowley was doing. He was pushing every protective instinct that Bobby had when it came to Dean and Sam. But then... it didn't matter. He'd already proved he was perfectly willing to risk his soul by avoiding his Reaper to have even a ghost – ha! – of a chance at protecting his boys. 

He wasn't about to quit doing his goddamned job just because he was in Hell.

Bobby looked at Crowley in the eyes, having made his decision. Crowley must have read it on his face because he snapped his fingers and the spell bindings loosed.

“Unless what?” Bobby gritted out, through clenched teeth. He resisted the urge to simply attack the demon, knowing it wouldn't do a goddamned thing. Here and now, he was outmatched and weaponless. And it wasn't like an exorcism would work when the demon was already back in Hell.

The knowing glance Crowley shot him, as if he knew that he could ask for anything and Bobby would give it to him, made Bobby cross his arms and raise his chin to take whatever he would dish out. 

“Well?” he asked impatiently. “I ain't got all day. I gotta lot of wall staring to catch up on.”

Crowley's mouth twitched up at the corners and laugh that followed rang of genuine amusement. “Bobby, Bobby, Bobby, haven't you guessed by now? I want you.”

Bobby blinked. “What? What in God's name are ya talking about?” he asked, both annoyed and baffled. What was the demon going on about? As he'd already crudely put it, Crowley owned his ass. He didn't need to bargain for it. 

“You know how Hell works, right?” Crowley gestured with his right hand to the entire room. “We take human souls, those who've sold it to us and those who've earned the trip down below. We take those bright and shiny souls and break them until they're demons. Which honestly, is a rather crude tactic that leaves them mostly useless and little better than cannon-fodder, but nevermind that.” Crowley's expression grew irritated. “It's a long process, it can take centuries to get a soul twisted just right – pardon me – just wrong enough and scrub them clean of those pesky memories of their human lives to get them... demonic.”

Bobby nodded. Yeah, he knew. He'd been expecting the same thing to happen to him, after all. “I still don't see what that has to do with this proposal of yours,” he said warily.

Crowley stood up from the desk and stalked towards Bobby. “It's very simple, darling. I don't have the patience to wait. Knowing you, it'll probably take a millennium before you forget about your human life and even more before you're an obedient, loyal servant of your King.” He leaned forward, his hands dropping onto Bobby's thighs like weights, or shackles. “So this is my proposal, I won't kill your precious Winchesters and you pledge your obedience to me.” His manicured nails dug into Bobby's flesh as if they were talons. “Which means, you say yes to _anything_ I want. I feel like letting off a little steam with some light torture, you get on the rack. I want to fuck you over my desk, you drop trou and whimper and _beg_ for more.” Crowley's heated eyes grew dreamy, “And call me a tiger in the sack. I love that.”

Bobby stared back at him disbelief. “This is a joke, right?”

Awareness snapped back into Crowley's eyes. His expression hardened. “No, Bobby Singer. I'm not joking.”

Jesus, Crowley was actually serious. Bobby swallowed, his mind turning the idea over. It was fucked up but if if would save his boys... Anything, he'd do anything. He stared back at Crowley without flinching. “I have a few conditions.”

Crowley blinked, and actually back off a step in his surprise at Bobby's audacity. Amusement softened the lines of his face. “Really? Well, I can be generous. I'll give you three so you better make them good.” He spread his arms. “Let's hear them.”

“You have to keep all demons away from them,” Bobby said firmly. “Just because you say you won't hurt them doesn't mean you won't order someone else to do your dirty work.” Crowley was a damned lawyer when it came to wording so he wasn't about to risk that again, not with his boys' lives on the line.

“Robert, you don't trust me? That hurts my black, shriveled heart.” Crowley raised both hands to his chest. Bobby shot him an irritated look for the dramatics. “Fine, fine. Neither I nor any of my demons will harm Sam and Dean Winchester, although I hold onto the right of self-defense if they come after me and mine.” Crowley raised his eyebrows and Bobby reluctantly nodded. “So what's your next demand,” the demon asked, a smirk curling up on his mouth. 

“No other demon can touch me.”

“Oh, I don't have a problem with that one. I don't share my toys and you're mine, Bobby Singer. I may have torn up the contract after you sold your soul to me but you were always _mine._ ”

The hell he was! Bobby ignored the disturbing possessive tone as much as possible as it pissed him off. “I mean even afterwards, if you decided to tear up this deal for any reason then I got back to my cell and no demon drags me off for a torture session.”

“Agreed,” Crowley said easily. “What's your last demand? I haven't exactly been knocked off my feet here, Bobby. Astonish me.”

Bobby paused and considered his last request. It felt right. Another way to protect those idjits now that he couldn't be up there with them. 

“Castiel is included.”

“What?!” Crowley thundered in incredulous rage. “The bloody angel is not a Winchester!”

Bobby set his mouth in a stubborn line. “Dean considers him family. The angel is included.”

“Just because that boy has got Castiel panting after him–”

“The idjit is a Winchester in all but name. He gets the same protection as Sam and Dean!”

Crowley snarled, low and guttural as he paced in front on him. As he watched him move back and forth radiating annoyance, Bobby worried that he'd pushed the demon too far and whether his boys would be dead because of it. The urge to take it back built up behind his teeth. 

Dammit, no. He couldn't afford to show any weakness. He had to stick to his guns.

Crowley came to abrupt stop and turned to face him. He was so mad he looked ready to chew nails and spit out rivets. “That bird is no fun to main, torture and kill when he's flying over the cuckoo's nest. Fine. Castiel is included with the provisions previously stated regarding Sam and Dean Winchester.” His expression became grudgingly appreciative.

A warm glow of satisfaction and relief blossomed in Bobby's chest. They'll be safe. Dean, Sam and Castiel would be safe from demons with this. It was better than anything Bobby could have hoped for short of him killing Crowley and every demon in Hell.

“Let's seal this deal, shall we?” Crowley reached for Bobby's shirt and used it to pull him to his feet with one hand. “Pucker up, darling. I'm feeling traditional.”

Bobby braced himself for the same slimy, devastating feeling he'd had the last time he'd sealed a deal with the demon and kissed Crowley again. He kept his tongue to himself this time too, no matter what the damned demon had said.

After a second of contact, Crowley surged forward, clamping his hands onto Bobby's head to hold him in place. He kissed like he was trying to devour Bobby, with his tongue in Bobby's mouth like it was an invading force. When he finally broke the lip-lock, Bobby was grateful that he didn't actually need to breathe anymore because he had the feeling that Crowley would've happily kept it up until Bobby passed out and maybe even until he suffocated.

He barely had to chance to appreciate no longer having a demon sucking his face when Crowley snapped his fingers. 

Bobby yelped as he reappeared in mid-air. He fell and bounced twice on the large bed he'd appeared over, before laying flat on his back. He was buck naked as the day he was born. To add insult to injury that demonic bastard had even taken off his cap.

Crowley appeared next to him, stretched out on his side. He was still fully dressed in his favorite black suit. His smile was smug and hungry, growing wider at the sight of Bobby. 

“Bobby Singer, what shall I do with you?” Crowley asked lightly. His eyes swept Bobby from head to toe and lingered back up again to pause at Bobby's groin. He licked his lips.

Bobby gritted his teeth and resisted the urge to hide. He had nothing to be ashamed of. He was a grown-ass man and he'd made his choice. 

“Oh, that's right,” Crowley purred, rolling over onto Bobby and pinning him down with a hand on his bare chest. “The answer is: absolutely anything I want. Now what do you say?”

Slowly, reluctantly but knowing it was inevitable, Bobby took a fortifying breath and said, “Yes.” 

End

**Author's Note:**

> So I've been rewatching the series – yes the whole thing – in anticipation of Season 9 when I got attacked by this plot bunny because the episode Taxi Driver baffled the hell out of me. Such as why didn't Crowley use the fact that he had Bobby's soul as leverage against Sam and Dean when he was pulling out all the stops to stop the Demon Tablet trials? Unless... he really wanted Bobby for his own. Seriously, can anyone give a better reason as to why Crowley never mentioned having Bobby's soul? And why Bobby after – just counting the 1 year jump – spent 160 + years in Hell and then came out of it mostly okay? Because otherwise this is my headcanon.


End file.
